US5332711A - Thermal transfer image-receiving sheet - Google Patents

Thermal transfer image-receiving sheet Download PDF

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Publication number
US5332711A
US5332711A US07/996,200 US99620092A US5332711A US 5332711 A US5332711 A US 5332711A US 99620092 A US99620092 A US 99620092A US 5332711 A US5332711 A US 5332711A
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US
United States
Prior art keywords
dye
thermal transfer
sheet
receiving
image
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US07/996,200
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English (en)
Inventor
Ryohei Takiguchi
Hitoshi Saito
Masanori Torii
Jun Hasegawa
Tetsuo Shiraiwa
Eriko Hayashi
Michiyuki Kono
Shigeo Mori
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dai Nippon Printing Co Ltd
DKS Co Ltd
Original Assignee
Dai Nippon Printing Co Ltd
Dai Ichi Kogyo Seiyaku Co Ltd
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Filing date
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Assigned to DAI-ICHI KOGYO SEIYAKU CO., LTD., DAI NIPPON PRINTING CO., LTD. reassignment DAI-ICHI KOGYO SEIYAKU CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: HASEGAWA, JUN, HAYASHI, ERIKO, KONO, MICHIYUKI, MORI, SHIGEO, SAITO, HITOSHI, SHIRAIWA, TETSUO, TAKIGUCHI, RYOHEI, TORII, MASANORI
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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/50—Recording sheets characterised by the coating used to improve ink, dye or pigment receptivity, e.g. for ink-jet or thermal dye transfer recording
    • B41M5/52—Macromolecular coatings
    • B41M5/5263—Macromolecular coatings characterised by the use of polymers obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • B41M5/5281—Polyurethanes or polyureas
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/913—Material designed to be responsive to temperature, light, moisture
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S428/00—Stock material or miscellaneous articles
    • Y10S428/914—Transfer or decalcomania
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]

Definitions

  • the present invention relates to a thermal transfer image-receiving sheet. More particularly, the present invention is concerned with a thermal transfer image-receiving sheet capable of forming a record image excellent in coloring density, sharpness and various types of fastness, particularly durability such as light fastness, fingerprint resistance and plasticizer resistance.
  • thermal transfer printing processes which comprises supporting a sublimable dye as a recording agent on a substrate sheet, such as a polyester film, to form a thermal transfer sheet and forming various full color images on an image-receiving sheet dyeable with a sublimable dye, for example, an image-receiving sheet comprising paper, a plastic film or the like and, formed thereon, a dye-receiving layer.
  • a thermal head of a printer is used as heating means, and a number of color dots of three or four colors are transferred to the image-receiving material by heating for a very short period of time, thereby reproducing a full color image of an original by means of the multicolor dots.
  • the color material used is a dye
  • the image thus formed is very clear and highly transparent, so that the resultant image is excellent in reproducibility and gradation of intermediate colors, and according to this method, the quality of the image is the same as that of an image formed by conventional offset printing and gravure printing, and it is possible to form an image having a high quality comparable to a full color photographic image.
  • thermal transfer sheet not only the construction of the thermal transfer sheet but also the construction of an image-receiving sheet for forming an image are important for usefully practicing the above-described thermal transfer process.
  • Japanese Patent Laid-Open Publication Nos. 169370/1982, 207250/1982 and 25793/1985 disclose prior art techniques applicable to the above-described thermal transfer image-receiving sheet, wherein the dye-receiving layer is formed by using a polyester resin, vinyl resins such as a polyvinyl chloride, a polycarbonate resin, a polyvinyl butyral resin, an acrylic resin, a cellulose resin, an olefin resin and a polystyrene resin.
  • vinyl resins such as a polyvinyl chloride, a polycarbonate resin, a polyvinyl butyral resin, an acrylic resin, a cellulose resin, an olefin resin and a polystyrene resin.
  • thermo transfer image-receiving sheet it is known that the dyeability of the dye-receiving layer and various types of durability and storage stability of an image formed thereon greatly vary depending upon the kind of the resin constituting the dye-receiving layer.
  • the dyeing capability of the dye which is transferred can be improved by improving the diffusivity of the dye at the time of the thermal transfer through the formation of the dye-receiving layer from a resin having a good dyeability or the incorporation of a plasticizer in the dye-receiving layer.
  • the dye-receiving layer comprising the above-described resin having a good dyeability, the formed image blurs during storage. Therefore, the storage stability is poor or the fixability of the dye is poor, so that the dye bleeds out on the surface of the image-receiving sheet, which causes other articles in contact with the surface of the sheet to be liable to staining.
  • Three-dimensional crosslinking of the resin layer for receiving a dye is considered as means for solving the above-described problems, and several proposals have been made on the three-dimensional crosslinking. Examples thereof include a method disclosed in Japanese Patent Laid-Open Nos. 215398/1983, 199997/1986, 34392/1990, 178089/1990 and 86494/1990 wherein the three-dimensional crosslinking is conducted by reacting a polyester resin with a polyisocyanate and a method disclosed in Japanese Patent Laid-Open Nos. 160681/1989, 123794/1989 and 126587/1991 wherein the three-dimensional crosslinking is conducted by reacting a vinyl chloride/vinyl acetate copolymer having active hydrogen with a polyisocyanate.
  • the amount of an active hydrogen having an isocyanate group, which can be introduced into one molecule is limited.
  • the proportion of the hydroxyl group in the case of a polyester resin, although the proportion of the hydroxyl group can be increased by reducing the molecular weight, the proportion of the hydroxyl group is necessarily low when the polyester resin has a commonly used molecular weight (a number average molecular weight of 10,000 or more).
  • a hydroxyl group in the case of a vinyl chloride/vinyl chloride acetate copolymer resin, although a hydroxyl group can be introduced by saponifying vinyl acetate monomer units, an increase in the proportion of the hydroxyl group (40% by mole or more) causes the copolymer to become insoluble in a general purpose solvent other than an alcohol. Therefore, the amount of introduction of the hydroxyl group should be reduced, which causes the crosslinking density of the dye-receiving layer to be low.
  • an object of the present invention is to provide a thermal transfer image-receiving sheet which can provide a clear image having a sufficiently high density and which is excellent in various types of fastness, particularly durability such as light fastness, fingerprint resistance and plasticizer resistance according to a thermal transfer printing process wherein use is made of a heat migratable dye such as a sublimable dye.
  • the present invention provides a thermal transfer image-receiving sheet comprising a substrate sheet and a dye-receiving layer formed on at least one surface of the substrate sheet, wherein said dye-receiving layer comprises a product of a reaction of a polyoxyalkylene polyol with an organic polyisocyanate.
  • thermo transfer image-receiving sheet which can provide a clear image having a sufficiently high density and which is excellent in various types of fastness, particularly durability such as light fastness, fingerprint resistance and plasticizer resistance.
  • the thermal transfer image-receiving sheet of the present invention comprises a substrate sheet and a dye-receiving layer formed on at least one surface of the substrate sheet.
  • the substrate sheet used in the present invention examples include synthetic paper (polyolefin, polystyrene and other synthetic paper), wood free paper, art paper, coat paper, cast coat paper, wall paper, paper for backing, paper impregnated with a synthetic resin or an emulsion, paper impregnated with a synthetic rubber latex, paper containing an internally added synthetic resin, fiber board, etc., cellulose fiber paper, and films or sheets of various plastics such as polyolefin, polyvinyl chloride, polyethylene terephthalate, polystyrene, polymethacrylate and polycarbonate.
  • a white opaque film or a foamed sheet prepared by adding a white pigment or filler to the above described synthetic resin and forming a film from the mixture or foaming the mixture.
  • a laminate comprising any combination of the above-described substrate sheets.
  • Typical examples of the laminate include a laminate comprising a combination of a cellulose fiber paper with a synthetic paper and a laminate comprising a combination of a cellulose fiber paper with a plastic film or sheet.
  • the thickness of these substrate sheets may be arbitrary and is generally in the range of from 10 to 300 ⁇ m.
  • the surface of the substrate sheet be subjected to a primer treatment or a corona discharge treatment.
  • the receiving layer formed on the surface of the substrate sheet serves to receive a sublimable dye moved from the thermal transfer sheet and to maintain the formed image.
  • the polyoxyalkylene polyol used in the present invention can be prepared, for example, by addition-polymerizing an alkylene oxide with an active hydrogen compound in the presence of a catalyst and removing the catalyst by a generally known purification method such as an ion-exchange method, a neutralization filtration method or an adsorption method and has a number average molecular weight of 200 to 10,000, preferably 200 to 5,000.
  • the active hydrogen compound examples include compounds having two or more active hydrogen groups, for example, polyhydric alcohols such as ethylene glycol, propylene glycol, 1,4-butanediol, glycerin, trimethylolpropane, pentaerythritol, dipentaerythritol, sorbitol, sucrose and tris-(2-hydroxyethyl) isocyanurate, amine compounds such as monoethanolamine, ethylenediamine, diethylenetriamine, 2-ethylhexylamine and hexamethylenediamine and phenolic active hydrogen compounds such as bisphenol A, hydroquinone and its hydrogenation product.
  • polyhydric alcohols such as ethylene glycol, propylene glycol, 1,4-butanediol, glycerin, trimethylolpropane, pentaerythritol, dipentaerythritol, sorbitol, sucrose and tris-(2-hydroxyethyl)
  • alkylene oxide examples include ethylene oxide, propylene oxide and buthylene oxide.
  • the polymerization may be any of a homopolymerization and a copolymerization and the addition may be conducted in any order.
  • a basic catalyst such as sodium methylate, sodium hydroxide or lithium carbonate
  • a Lewis acid catalyst such as boron trifluoride
  • an amine catalyst such as trimethylamine or triethylamine.
  • the amount of use of the catalyst may be substantially the same as that generally adopted in the art.
  • polyoxyalkylene polyol examples include compounds represented by the following structural formulae A to E. ##STR1## wherein R stands for --C 2 H 4 --, ##STR2## P stands for CH 2 CH 3 or CH 2 O--(--RO--) n --H and n is a numeric value capable of providing a number average molecular weight of 200 to 5,000.
  • organic polyisocyanate used in the crosslinking of the above-described polyol examples include 2,4-tolylene diisocyanate (2,4-TDI), 2,6-tolylene diisocyanate (2,6-TDI), 4,4'-diphenylmethane diisocyanate (MDI), hexamethylene diisocyanate (HMDI), isophorone diisocyanate (IPDI), triphenylmethane tridiisocyanate, tris(isocyanatephenyl) thiophosphate, lysine ester triisocyanate, 1,8-diisocyanato-4-isocyanate methyloctane, 1,6,11-undecane triisocyanate, 1,3,6-hexamethylene triisocyanate, bicycloheptane triisocyanate and further compounds called "isocyanate adduct" such as biuret-bonded HMDI, isocyanurate--bonded HMDI and
  • the use of a catalyst is advantageous.
  • the catalyst include organic metal catalysts such as dibutyl tin dilaurate (DBTDL), dibutyl tin diacetate (DBTA), phenyl mercury propionate and lead octenoate and amine catalysts such as triethyelendiamine, N,N'-dimethylpiperadine, N-methylmorpholine, tetramethylguanidine and triethylamine.
  • polyurethane resins may be used alone or in the form of a mixture of two or more of them. Further, it is also possible to use them in combination with other thermoplastic resins, for example, polyolefin resins such as polypropylene, halogenated polymers such as polyvinyl chloride and polyvinylidene chloride, vinyl polymers such as polyvinyl acetate, polyacrylic ester and polyvinyl acetal, polyester resins such as polyethylene terephthalate and polybutylene terephthalate, polystyrene resin, polyamide resin, copolymer resins comprising an olefin, such as ethylene or propylene, and other vinyl monomer, ionomers, cellulosic resins such as cellulose diacetate and polycarbonate.
  • polyolefin resins such as polypropylene, halogenated polymers such as polyvinyl chloride and polyvinylidene chloride, vinyl polymers such as polyvinyl acetate,
  • the thermal transfer image-receiving sheet according to the present invention can be produced by coating at least one surface of the above-described substrate sheet with a suitable organic solvent solution or water or organic solvent dispersion of the above described polycarbonate resin and optionally containing necessary additives, for example, a release agent, a crosslinking agent, a curing agent, a catalyst, a heat release agent, an ultraviolet absorber, an antioxidant and a photostabilizer, for example, by a gravure printing method, a screen printing method or a reverse roll coating method wherein use is made of a gravure print, and drying the resultant coating to form a dye-receiving layer.
  • a suitable organic solvent solution or water or organic solvent dispersion of the above described polycarbonate resin and optionally containing necessary additives, for example, a release agent, a crosslinking agent, a curing agent, a catalyst, a heat release agent, an ultraviolet absorber, an antioxidant and a photostabilizer, for example, by a gravure printing method, a screen
  • the receiving layer it is possible to add pigments or fillers such as titanium oxide, zinc oxide, kaolin clay, calcium carbonate and finely divided silica for the purpose of further enhancing the sharpness of a transferred image through an improvement in the whiteness of the receiving layer.
  • pigments or fillers such as titanium oxide, zinc oxide, kaolin clay, calcium carbonate and finely divided silica for the purpose of further enhancing the sharpness of a transferred image through an improvement in the whiteness of the receiving layer.
  • the thickness of the dye-receiving layer formed by the above-described method may be arbitrary, it is generally in the range of from 1 to 50 ⁇ m. It is preferred for the dye-receiving layer to comprise a continuous coating. However, the dye-receiving layer may be formed as a discontinuous coating through the use of a resin emulsion or a resin dispersion.
  • the image-receiving sheet of the present invention can be applied to various applications where thermal transfer recording can be conducted, such as cards and sheets for preparing transparent originals, by properly selecting the substrate sheet.
  • a cushion layer may be optionally provided between the substrate sheet and the receiving layer, and the provision of the cushion layer enables an image less susceptible to noise during printing and corresponding to image information to be formed by transfer recording with good reproducibility.
  • a resin for the cushion layer a polyurethane, a polybutadiene, a polyacryiate, a polyester, an epoxy resin, a polyamide, a rosin-modified phenol, a terpene phenol resin or an ethylene/vinylacetate copolymer or a mixture thereof can be employed.
  • the thermal transfer sheet for use in the case where thermal transfer is conducted through the use of the above-described thermal transfer sheet of the present invention comprises a paper or a polyester film and, provided thereon, a dye layer containing a heat migratable dye such as a sublimable dye, and any conventional thermal transfer sheet, as such, may be used in the present invention.
  • Means for applying thermal energy at the time of the thermal transfer may be any means known in the art.
  • a desired object can be sufficiently attained by applying a thermal energy of about 5 to 100 mJ/mm 2 through the control of a recording time by means of a recording device, for example, a thermal printer (for example, a video printer VY-100 manufactured by Hitachi, Limited).
  • Synthetic paper (thickness: 100 ⁇ m; a product of Oji-Yuka Synthetic Paper Co., Ltd.) was used as the substrate sheet, and a coating solution having the following composition was coated and dried by means of a wire bar on one surface of the synthetic paper so that the coverage on a dry basis was 5.0 g/m 2 , and the resultant coating was cured at 120° C. for 30 minutes to provide thermal transfer image-receiving sheets of the present invention.
  • an ink composition for forming a dye-supporting layer was prepared according to the following formulation, coated by means of a wire bar on a 6 ⁇ m-thick polyethylene terephthalate film having a reverse face subjected to a treatment for rendering the face heat-resistant so that the coverage on a dry basis was 1.0 g/m 2 , and the resultant coating was dried to provide a thermal transfer sheet.
  • the above-described thermal transfer sheet and the above-described thermal transfer image-receiving sheet of the present invention were put on top of the other in such a manner that the dye layer and the dye receiving surface faced each other. Recording was conducted by means of a thermal head from the back surface of the thermal transfer sheet under conditions of a head applied voltage of 11.0 V, a pulse width of 16 msec and a dot density of 6 dots/line, and the results are given in the following Table 2. Various types of durability given in Table 2 were evaluated by the following methods.
  • ⁇ :Retention 90% or more.
  • ⁇ :Retention was 80% to 90% exclusive.
  • ⁇ :Retention was 70% to 80% exclusive.
  • X:Retention was less than 70%.
  • a finger was pressed against the surface of the print to leave a fingerprint, and the print was allowed to stand at room temperature for 5 days. Then, the discoloration and change in the density of the fingerprinted portion was evaluated with the naked eye.
  • Example 1 The procedure of Example 1 was repeated to form a comparative thermal transfer image-receiving sheet, except that, in the composition of the coating solution of Example 1, polyoxyalkylene polyol and polyisocyanate and their proportions were changed as follows.
  • Comparative Example 1 The procedure of Comparative Example 1 was repeated to form a comparative thermal transfer image-receiving sheet, except that polyisocyanate was omitted from the composition used in Comparative Example 1.
  • a product of a reaction of a polyoxyalkylene polyol with an organic polyisocyanate resin is used as a resin component for the formation of a dye-receiving layer, it becomes possible to provide a thermal transfer image-receiving sheet which can form a sharp image having a sufficient density and excellent in various types of fastness, particularly durability such as light fastness, fingerprint resistance and plasticizer resistance.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Thermal Transfer Or Thermal Recording In General (AREA)
US07/996,200 1991-12-27 1992-12-22 Thermal transfer image-receiving sheet Expired - Lifetime US5332711A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP3-358240 1991-12-27
JP35824091A JPH0615966A (ja) 1991-12-27 1991-12-27 熱転写受像シート

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US5332711A true US5332711A (en) 1994-07-26

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US (1) US5332711A (ja)
EP (1) EP0550876B1 (ja)
JP (1) JPH0615966A (ja)
DE (1) DE69204646T2 (ja)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6225381B1 (en) * 1999-04-09 2001-05-01 Alliedsignal Inc. Photographic quality inkjet printable coating
KR102071641B1 (ko) * 2018-11-27 2020-01-30 주식회사 마이팝 열 승화 전사성 코팅액 및 이를 이용한 폴리우레탄 인공피혁에 전사물을 열 승화 전사시키는 방법

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4421826A (en) * 1980-05-08 1983-12-20 W. R. Grace & Co. Polyurethane polymer amine salt as a dyeing aid, particularly for polyolefin fibers

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4421826A (en) * 1980-05-08 1983-12-20 W. R. Grace & Co. Polyurethane polymer amine salt as a dyeing aid, particularly for polyolefin fibers

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Database WPIL, No. 86 200667, Derwent Publications Ltd; London, GB; JP A 61132367 (Dai Nippon Pringing) Jun. 19, 1986. *
Database WPIL, No. 86-200667, Derwent Publications Ltd; London, GB; JP-A-61132367 (Dai Nippon Pringing) Jun. 19, 1986.

Also Published As

Publication number Publication date
EP0550876B1 (en) 1995-09-06
DE69204646T2 (de) 1996-06-05
DE69204646D1 (de) 1995-10-12
EP0550876A1 (en) 1993-07-14
JPH0615966A (ja) 1994-01-25

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